US11952361B1ActiveUtility

2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl) pyridin-3-ol as an antitumor and antimicrobial compound

Assignee: UNIV KING FAISALPriority: Dec 26, 2023Filed: Dec 26, 2023Granted: Apr 9, 2024
Est. expiryDec 26, 2043(~17.4 yrs left)· nominal 20-yr term from priority
C07D 401/04A61P 35/00
69
PatentIndex Score
0
Cited by
8
References
7
Claims

Abstract

A compound 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol compound, its synthesis, and its use as an anticancer, anti-inflammatory, and/or antimicrobial agent.

Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A method of making 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol, the method comprising:
 adding benzil, 6-hydroxypyridine-2-carbaldehyde, ammonium acetate, and N,N-dimethyl-3-aminopropane to piperidinium hydrogen sulfate in an oil bath to obtain a reaction mixture; 
 heating the reaction mixture with stirring until reaction completion to obtain a crude product; 
 purifying the crude product by recrystallization using absolute ethyl alcohol; and 
 obtaining the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol compound. 
 
     
     
       2. The method of making the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol of  claim 1 , wherein the oil bath is at a temperature of about 25° C. to about 35° C. 
     
     
       3. The method of making the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol of  claim 1 , wherein heating is at a temperature of about 100° C. 
     
     
       4. The method of making the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol of  claim 1 , wherein after reaction completion the reaction mixture is washed with water. 
     
     
       5. The method of making the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol of  claim 1 , wherein the benzil, 6-hydroxypyridine-2-carbaldehyde, and ammonium acetate are added in an about 1:1:1 molar ratio. 
     
     
       6. The method of making the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol of  claim 1 , wherein the benzil, 6-hydroxypyridine-2-carbaldehyde, ammonium acetate, N,N-dimethyl-3-aminopropane are added in an about 1:1:1:0.5 molar ratio. 
     
     
       7. The method of making the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol of  claim 1 , wherein the 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol compound is obtained in an about 95% yield.

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